Fluorinated acrylate derivatives having carbonate groups and polymerizable composition comprising same

Abstract

A polymerizable composition comprising a novel carbonate group-containing acrylate derivative of formula (I) of the present invention is used to prepare a polymer film or molded product having improved compatibility with dyes, high adhesivity to a substrate, low optical loss and low birefringence: wherein: n is an integer of 1 to 4; R 1 is hydrogen or C 1-3 alkyl; R 2 is —(CH 2 ) a O— or —(CH 2 CH 2 O) b — (a is an integer of 1 to 20, and b is an integer of 2 to 20); R 3 is an optional substituent selected from the group consisting of —CH 2 —, —C 6 H 4 — and —C 6 F 4 —; and R 4 is C 1-10 perfluoroalkyl when n=1; when n=2, a bridging group comprising at least one linking moiety selected from the group consisting of C 1-3 perfluoroalkylene, C 1-3 perfluoroalkyleneoxy and —CF 2 CFCl—; or when n=3 or 4, a bridging group comprising and said linking moiety.

What is claimed is:  
     
         1 . A fluorinated acrylate derivative of formula (I):  
       
         
           
           
               
               
           
         
       
       wherein: 
 n is an integer of 1 to 4;  
 R 1  is hydrogen or C 1-3  alkyl;  
 R 2  is —(CH 2 ) a O— or —(CH 2 CH 2 O) b — (a is an integer of 1 to 20, and b is an integer of 2 to 20);  
 R 3  is an optional substituent selected from the group consisting of —CH 2 —, —C 6 H 4 — and —C 6 F 4 —; and  
 R 4  is C 1-10  perfluoroalkyl when n=1; when n=2, a bridging group comprising at least one linking moiety selected from the group consisting of C 1-3  perfluoroalkylene, C 1-3  perfluoroalkyleneoxy and —CF 2 CFCl—; or when n=3 or 4, a bridging group comprising  
                     
 and said linking moiety.  
 
     
     
         2 . A process for preparing the compound of  claim 1  which comprises reacting a compound of formula (II) with a compound of formula (III) in an organic solvent in the presence of a base:  
       
         
           
           
               
               
           
         
       
       wherein: 
 R 1 , R 2 , R 3 , R 4  and n have the same meanings as defined in  claim 1 .  
 
     
     
         3 . The process of  claim 2 , wherein the reaction is conducted at a temperature ranging from 0 to 150° C. for 30 minutes to 14 days using a base selected from the group consisting of triethylamine, diisopropylamine, tetramethyl ethylenediamine, pyridine, tetrabutylammonium bromide, benzyltrimethylammonium chloride, KOH, K 2 CO 3  and a mixture thereof, and an organic solvent selected from the group consisting of chloroform, methylene chloride, tetrahydrofuran, N-methylpyrrolidone, methylsulfoxide, N,N-dimethylacetamide, 1,4-dioxane, ethylalcohol, methylalcohol, benzene, ethylene glycol dimethyl ether, acetonitrile and a mixture thereof.  
     
     
         4 . A polymerizable composition comprising the compound of  claim 1  as a polymerizable monomer and a polymerization initiator.  
     
     
         5 . The composition of  claim 4  which further comprises an additional hydrocarbon monomer, or an oligomer or polymer thereof.  
     
     
         6 . A polymer film prepared by coating the composition of  claim 4  on a substrate, followed by heat- or photo-curing.  
     
     
         7 . A molded product prepared by placing the composition of  claim 4  in a mold, followed by heat- or photo-curing.